# US 2023/0053941 A1 · Microemulsions with dicamba salts having improved properties > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2023/0053941 A1 - Document ID: US20230053941A1 - Status: Published application - Kind: A1 - Application number: 17/792,611 - Filed: 2021-01-14 - Published: 2023-02-23 - Earliest claimed: 2020-01-17 - Assignees: Monsanto Technology LLC - Applicants: Monsanto Technology LLC - Inventors: Ganiyu JIMOH - Web page: https://patentgrep.com/patent/US20230053941A1 ## CPC - A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines - A01N 25/04: Dispersions, {emulsions, suspoemulsions, suspension concentrates} or gels (foams A01N25/16) - A01N 37/40: having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system - A01N 57/20: containing acyclic or cycloaliphatic radicals - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS ## Abstract The present invention relates to the technical field of crop protection. The present invention primarily relates to herbicide compositions in the form of a microemulsion comprising as compound (A) ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate and as compound (B) one or more dicamba salts, in particular to herbicidal microemulsion containing further constituents, said microemulsions having improved properties. The invention also relates to methods of manufacturing such microemulsions and the use of such microemulsions. ## Claims ### Claim 1 A herbicide composition in the form of an oil-in-water microemulsion comprising compounds (A) and (B), wherein: (A) denotes ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate; and (B) denotes one or more dicamba salts. ### Claim 2 (depends on 1) The herbicide composition as claimed in claim 1, wherein compound (B) is selected from the group consisting of the tetrabutylamine salt of dicamba, the dimethylamine salt of dicamba, the isopropylamine salt of dicamba, the diglycolamine salt of dicamba, the N,N-bis-(3-aminopropyl)methylamine salt of dicamba, the choline salt of dicamba, the monoethanolamine salt of dicamba, the diethanolamine salt of dicamba, the triethanolamine salt of dicamba, the potassium salt of dicamba, and the sodium salt of dicamba. ### Claim 3 (depends on 1) The herbicide composition as claimed in claim 1, wherein the ratio by weight of the total amount of compound (A) and the total amount of compound (B) is in the range of from about 1:1 to 1:100. ### Claim 4 (depends on 1) The herbicide composition as claimed in claim 1, comprising compound (B) in a total amount of up to about 65 wt.-%, based on the total weight of the herbicide composition. ### Claim 5 (depends on 1) The herbicide composition as claimed in claim 1, further comprising one or more further constituents selected from the group consisting of other herbicidal active compounds, herbicide safeners, formulation auxiliaries and additives customary in crop protection. ### Claim 6 (depends on 5) The herbicide composition as claimed in claim 5, wherein the additionally present herbicidal active compound is selected from the group consisting of glyphosate and salts thereof. ### Claim 7 (depends on 1) The herbicide composition as claimed in claim 1, further comprising at least one dispersant, preferably one or more dispersants selected from the group consisting of phosphate esters and/or one or more alkylpolyglucosides. ### Claim 8 (depends on 1) The herbicide composition as claimed in claim 1, further comprising a substantially water-immiscible organic solvent, wherein the organic solvent is preferably selected such that compound (A) has an organic solvent/water partition coefficient, expressed as a logarithm, of about 4 or greater. ### Claim 9 (depends on 1) The herbicide composition as claimed in claim 1, further comprising one or more water-soluble stabilizing agents. ### Claim 10 (depends on 1) The herbicide composition as claimed in claim 1, further comprising one or more water-soluble stabilizing agents selected from the group consisting of inorganic halides, wherein the stabilizing agent is present in a concentration sufficient to provide a concentration of halide ions of from about 0.5% to about 2.5% by weight, based on the total weight of the composition. ### Claim 11 (depends on 1) The herbicide composition as claimed in claim 1, further comprising one or more mono carboxylic acids and/or salts thereof. ### Claim 12 (depends on 1) The herbicide composition as claimed in claim 1, wherein the pH-value of a diluted composition is less than 7, when diluted with water such that the concentration of the dicamba salt corresponds to 1.2% by weight calculated as dicamba acid and measured at 25° C. and 1013 mbar. ### Claim 13 (depends on 1) The herbicide composition as claimed in claim 1, further comprising a drift retardant agent. ### Claim 14 (depends on 1) The herbicide composition as claimed in claim 1, wherein compound (B) is selected from the group consisting of the diglycolamine salt of dicamba, the N,N-bis-(3-aminopropyl)methylamine salt of dicamba, the monoethanolamine salt of dicamba, the diethanolamine salt of dicamba and the triethanolamine salt of dicamba. ### Claim 15 (depends on 1) A method for controlling undesired plant growth, comprising applying the herbicide composition as defined in claim 1 onto the plants, parts of plants, plant seeds or the area where the plants grow. ### Claim 16 (depends on 1) The use of the herbicide composition defined in claim 1 for controlling harmful plants. ### Claim 17 (depends on 1) A method of manufacturing the herbicide composition defined in claim 1, comprising the following steps: (i) providing water and optionally one or more stabilizing agents; (ii) providing compound (B); (iii). providing compound (A) dissolved in one or more organic solvents, wherein (a) at least one of said organic solvents is not fully miscible with water and wherein (b) compound (A) has a solubility of 5 wt.-% or greater, in at least one of said organic solvents, measured at 25° C. and 1013 mbar; mixing the constituents provided in steps (i), (ii) and (iii). ### Claim 18 (depends on 1) The herbicide composition as claimed in claim 1, comprising compound (B) in a total amount in the range from about 10 wt.-% to about 65 wt.-%, based on the total weight of the herbicide composition. ### Claim 19 (depends on 18) The herbicide composition as claimed in claim 18, further comprising one or more further constituents selected from the group consisting of other herbicidal active compounds, herbicide safeners, formulation auxiliaries and additives customary in crop protection. ### Claim 20 (depends on 19) The herbicide composition as claimed in claim 19, wherein the additionally present herbicidal active compound is selected from the group consisting of glyphosate and salts thereof. ### Claim 21 (depends on 1) The herbicide composition as claimed in claim 1, further comprising at least one dispersant selected from the group consisting of phosphate esters and/or one or more alkylpolyglucosides. ### Claim 22 (depends on 18) The herbicide composition as claimed in claim 18, further comprising a substantially water-immiscible organic solvent, wherein the organic solvent is preferably selected such that compound (A) has an organic solvent/water partition coefficient, expressed as a logarithm, of about 4 or greater. ### Claim 23 (depends on 18) The herbicide composition as claimed in claim 18, further comprising one or more water-soluble stabilizing agents. ### Claim 24 (depends on 1) The herbicide composition as claimed in claim 1, further comprising one or more water-soluble stabilizing agents selected from the group consisting of inorganic halides, wherein the stabilizing agent is present in a concentration sufficient to provide a concentration of halide ions of from about 0.5% to about 2.5% by weight, based on the total weight of the composition. ### Claim 25 (depends on 1) The herbicide composition as claimed in claim 1, further comprising one or more C1-C4-alkyl mono carboxylic acids and/or salts thereof. ### Claim 26 (depends on 1) The herbicide composition as claimed in claim 1, wherein the pH-value of a diluted composition is in the range of about 4.5 to about 6.0 when the composition is diluted with water such that the concentration of the dicamba salt corresponds to 1.2% by weight calculated as dicamba acid and measured at 25° C. and 1013 mbar. ### Claim 27 (depends on 1) The herbicide composition as claimed in claim 1, further comprising a drift retardant agent selected from one or more fatty oils in a total amount in the range of about 1 wt.-% to about 10 wt. % based on the total weight of the composition. ### Claim 28 (depends on 18) The herbicide composition as claimed in claim 18, wherein compound (B) is selected from the group consisting of the diglycolamine salt of dicamba, the N,N-bis-(3-aminopropyl)methylamine salt of dicamba, the monoethanolamine salt of dicamba, the diethanolamine salt of dicamba and the triethanolamine salt of dicamba. ### Claim 29 (depends on 18) A method for controlling undesired plant growth, comprising applying the herbicide composition as defined in claim 18 onto the plants, parts of plants, plant seeds or the area where the plants grow. ### Claim 30 (depends on 18) The use of the herbicide composition defined in claim 18 for controlling harmful plants. ### Claim 31 (depends on 1) A method of manufacturing the herbicide composition defined in claim 1, comprising the following steps: (i) providing water and optionally one or more stabilizing agents; (ii) providing compound (B); (iii). providing compound (A) dissolved in one or more organic solvents, wherein (a) at least one of said organic solvents is not fully miscible with water and wherein (b) compound (A) has a solubility of 5 wt.-% or greater, in at least one of said organic solvents, measured at 25° C. and 1013 mbar; mixing the constituents provided in steps (i), (ii) and (iii).